Artwork

Content provided by Joubin Mirzadegan. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Joubin Mirzadegan or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.
Player FM - Podcast App
Go offline with the Player FM app!

#171 Founder and Former CEO Drift, David Cancel: Never Trapped

1:13:08
 
Share
 

Manage episode 392852212 series 2662695
Content provided by Joubin Mirzadegan. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Joubin Mirzadegan or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

Guest: David Cancel, founder and former CEO of Drift; founder of Rey

After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel trapped … Someone telling me, ‘you can’t leave,’ I was like, boom. Switch went off in my head … and I was like, ‘I’m out.’” The filing was ultimately delayed and David was able to quit just before the IPO; one day later, he started his next company, Drift.

In this episode, David and Joubin discuss the accountability of doing something, creating constraints, the Whitney Museum, imposter syndrome, Tony Hawk, John Romero, wandering without a map, conservative spending, Brian Halligan and Dharmesh Shah, Phil Jackson, the voices in your head, Shlomo Kramer, righteous independence, cancel culture and diversity, gut vs. data, and killing ideas with discipline.

In this episode, we cover:

  • Action and distractions (00:50)
  • Observer and outsider (05:36)
  • Advising entrepreneurs (11:18)
  • “It has to be bigger” (13:23)
  • David’s new company, Rey (16:38)
  • Remote vs. in-person work (21:24)
  • Who David will hire first (25:39)
  • Fundraising and bootstrapping (27:39)
  • The timeline for Rey (31:48)
  • Rebuilding Hubspot’s code base (33:36)
  • Leaving HubSpot at the IPO (42:54)
  • “You’re not done” (48:19)
  • HubSpot’s infamous exec meetings (54:44)
  • David’s hardest year and selling Drift (59:26)
  • The upmarket mistake (01:03:13)
  • Saying no to good ideas (01:08:12)
  • What “grit” means to David (01:11:52)

Links:

  continue reading

196 episodes

Artwork
iconShare
 
Manage episode 392852212 series 2662695
Content provided by Joubin Mirzadegan. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Joubin Mirzadegan or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

Guest: David Cancel, founder and former CEO of Drift; founder of Rey

After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel trapped … Someone telling me, ‘you can’t leave,’ I was like, boom. Switch went off in my head … and I was like, ‘I’m out.’” The filing was ultimately delayed and David was able to quit just before the IPO; one day later, he started his next company, Drift.

In this episode, David and Joubin discuss the accountability of doing something, creating constraints, the Whitney Museum, imposter syndrome, Tony Hawk, John Romero, wandering without a map, conservative spending, Brian Halligan and Dharmesh Shah, Phil Jackson, the voices in your head, Shlomo Kramer, righteous independence, cancel culture and diversity, gut vs. data, and killing ideas with discipline.

In this episode, we cover:

  • Action and distractions (00:50)
  • Observer and outsider (05:36)
  • Advising entrepreneurs (11:18)
  • “It has to be bigger” (13:23)
  • David’s new company, Rey (16:38)
  • Remote vs. in-person work (21:24)
  • Who David will hire first (25:39)
  • Fundraising and bootstrapping (27:39)
  • The timeline for Rey (31:48)
  • Rebuilding Hubspot’s code base (33:36)
  • Leaving HubSpot at the IPO (42:54)
  • “You’re not done” (48:19)
  • HubSpot’s infamous exec meetings (54:44)
  • David’s hardest year and selling Drift (59:26)
  • The upmarket mistake (01:03:13)
  • Saying no to good ideas (01:08:12)
  • What “grit” means to David (01:11:52)

Links:

  continue reading

196 episodes

All episodes

×
 
Loading …

Welcome to Player FM!

Player FM is scanning the web for high-quality podcasts for you to enjoy right now. It's the best podcast app and works on Android, iPhone, and the web. Signup to sync subscriptions across devices.

 

Quick Reference Guide